Bromine → 5-fluoro-4-methoxy-3-bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 75035Notes

Reaction equation

[F:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[Br:23]Br>C(Cl)(Cl)Cl.O>[F:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]2[C:10]([Br:23])=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.) solution of 5-fluoro-4-methoxy-1-tosyl-1H-pyrrolo[2,3-b]pyridine, 68b, (0.79 g, 2.45 mmol) in chloroform (50 mL) was added bromine (0.13 mL, 2.45 mmol). The reaction mixture was stirred at 0° C. for 3 hours and then slowly warmed to ambient temperature. The mixture was diluted with deionized water and quenched with aqueous sodium bicarbonate. The aqueous phase was extracted with methylene chloride and dried over sodium sulfate. The resulting solid was purified via silica gel chromatography (15-30% EtOAc/Hexanes) to give 170 mg of the desired product.

Workup

temperatureslowly warmed to ambient temperature
customquenched with aqueous sodium bicarbonate
extractionThe aqueous phase was extracted with methylene chloride
dry with materialdried over sodium sulfate
customThe resulting solid was purified via silica gel chromatography (15-30% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-d114db063dde45f7909760aa2c12cdae
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829007B2

Reaction notes

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